Sodium Hydroxide → HCID 178443467, compound

HRID 1030571Notes

Reaction equation

HRID 1030571 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([SH:9])[NH:8][C:4]=2[CH:3]=1.[OH-].[Na+].[CH2:14](Cl)/[CH:15]=[C:16](/[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])\[CH3:17]>CO>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7]([S:9][CH2:14]/[CH:15]=[C:16](\[CH3:17])/[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])=[N:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6372219Geranyl chlorideHCID 178527787HCID 178527787, compound

Product 1

HCID 178443467HCID 178443467, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the 5-chloro-2-mercaptobenzimidazole (0.665 g, 3.6 mmol) in methanol (10 mL) and 2N NaOH (7 mmol) was added geranyl chloride (0.775 g, 4.5 mmol). The reaction mixture was stirred at ambient temperature for 24 hours, evaporated in vacuo, dissolved in CH2Cl2, washed with water, and dried over Na2SO4. Evaporation and flash chromatography (Merck Kieselgel, CH2Cl2) gave an oil which was crystallized with pentane to yield a white solid of the title compound (270 mg). m.p. 102°-104° C. NMR (CDCl3)δ7.45-7.0(m,3H), 5.37(t, J=7 Hz,1H), 5.03(t,J=7Hz, 1H), 3.93(d,J=8 Hz,2H), 2.02(m,4H), 1.67(s,3H), 1.66(s,3H), 1.58(s,3H).

Workup

  1. customevaporated in vacuo
  2. dissolutiondissolved in CH2Cl2
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. customEvaporation and flash chromatography (Merck Kieselgel, CH2Cl2)
  6. customgave an oil which
  7. customwas crystallized with pentane

Sources & evidence

ORD record
ord-01295500dae14294a14fe532383b84bd
Source dataset
uspto-grants-1992_04
Patent number
US05106863

Reaction notes

Loading…